European Patent Application No. EP-A-0192060 (Nihon) relates to heterocyclic compounds of a general formula ##STR2## wherein: n is 0 or 1; A.sup.1, A.sup.2, A.sup.5 and A.sup.6 independently are hydrogen or alkyl; A.sup.3 and A.sup.4 independently are hydrogen, hydroxy or alkyl;
X is sulfur, oxygen, -N-A.sup.7 or -N-A.sup.8, wherein A.sup.7 is selected from a large group comprising, for example, hydrogen, halogen, hydroxy, alkoxy, benzyloxy or alkyl, and wherein A.sup.8 is selected from hydrogen, alkyl, aryl, or benzyl; PA1 Y is nitrogen or ##STR3## wherein A.sup.9 is selected from a large group comprising, for example, hydrogen, halogen, hydroxy, alkoxy, benzyloxy, or alkyl; PA1 A is hydrogen or alkyl; PA1 Z is a 5 or 6 membered heterocyclic group containing at least one heteroatom selected from oxygen, sulfur or nitrogen and at least one substituent selected from a large group comprising, for example, halogen, alkyl, haloalkyl, nitro, cyano, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkenyl, haloalkoxy, haloalkylthio, haloalkenyl, acylamino, haloacylamino, alkoxycarbonyl, thiocyanato or alkynyl. PA1 Q is a linkage group of the formula --CHR.sup.2 -- or CHR.sup.3 --CHR.sup.4 -- where R.sup.2 is hydrogen or alkyl, R.sup.3 is hydrogen or alkyl, and R.sup.4 is hydrogen or alkyl; PA1 X is nitrogen or .dbd.CH--; and PA1 Z is halogen. PA1 An alkyl group as referred to above is preferably a C.sub.1-4 alkyl group, more preferably a methyl group. PA1 R.sup.2 preferably is hydrogen or methyl and most preferably is hydrogen. PA1 R.sup.3 preferably is hydrogen. PA1 R.sup.4 preferably is hydrogen. PA1 Preferably, Q is --CHR.sup.2 -- where R.sup.2 is as defined above. PA1 Preferably, X is .dbd.CH--. PA1 Preferably, Z is bromine or chlorine, most preferably chlorine.
EP-A-0192060 purports to disclose 887 compounds but only a relatively few are accompanied by any physico-chemical data showing that they have been prepared.
The broad claims of EP-A-0192060 embrace the N-(3-halo-5-isoxazolylmethyl-2-nitromethylene- and 2-nitroimino imidazolines and pyrimidines of the present invention. Furthermore, three such compound structures are illustrated, on page 164, as Examples 522-524, as are several other 3-substituted-5-isoxazolylmethyl analogs, by means of a general formula and a tabular listing. ##STR4## However, there are no analytical or biological data provided with regard to such compounds and there is no indication that the compounds 522-524 were actually prepared or evaluated.
N-(3-Halo-5-isoxazolylmethyl)-2-nitromethylene- and -2-nitroimino imidazolines and pyrimidines and the properties thereof are therefore not properly enabled by the disclosure of EP-A-0192060.
The 3-methyl and 3-trifluoromethyl-5-isoxazolylmethyl compounds which are Examples 6, 519, and 529 in the Nihon application and which evidently were prepared have been made and tested but have been found to be less active in combating certain undesired pests than corresponding 3-halo-5-isoxazolyl compounds of the present invention.